Despite the central role of organized groups as intermediary bodies in American society, the constitutional right of association is surprisingly recent and limited. As the Supreme Court struggles to define the bounds of 'the' freedom of association, it is time to take a critical look at a difficult set of questions. First, many private organizations engage in various types of selection criteria, but what subjects the Jaycees to State anti-discrimination laws but insulates the Boy Scouts of America? Second, the typical American nonprofit organization is a corporation that lacks both shareholders and members, so are there any 'associates' whose rights are entitled to protection, or is the corporation's freedom of speech all that constitutionally matters? Third, regardless of whether an organization comprises members, not all (few?) private entities operate 'democratically'; does the law care? Finally, even if voice is democratic, how do we protect dissenters if exit is not voluntary? As we examine the structure for regulation of association and the role of the courts, we will appreciate the limits of the law in remedying private discriminatory and anti-democratic behavior. In general, the associational jurisprudence draws from our broader political structure that enshrines individual autonomy as its core norm. This Article does not, however, attempt to set out a normative prescription for creating political and moral values. For every advocate of group rights and group autonomy is an advocate of individual autonomy and protection from group tyranny. In the end, the debate leads me to caution that while we have a social and political obligation to exercise vigilance over how associations form and operate, we must recognize that our fundamental constitutional norms protect the rights of organizational autonomy in governance and functioning. The greatest challenge to a liberal society –a topic beyond the scope of this Article – will be whether and how to protect the rights of minority members of illiberal groups.